Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 21:51:16 UTC |
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Update Date | 2022-03-07 02:55:01 UTC |
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HMDB ID | HMDB0036688 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Costunolide |
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Description | Costunolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Costunolide. |
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Structure | C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1 InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5-,11-9- |
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Synonyms | Value | Source |
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Costunlide | HMDB | Costunolid | HMDB | Costus lactone | HMDB | Isocostunolide | MeSH | Costunolide | MeSH |
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Chemical Formula | C15H20O2 |
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Average Molecular Weight | 232.3181 |
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Monoisotopic Molecular Weight | 232.146329884 |
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IUPAC Name | 6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one |
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Traditional Name | 6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one |
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CAS Registry Number | 553-21-9 |
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SMILES | C\C1=C\CC\C(C)=C/C2OC(=O)C(=C)C2CC1 |
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InChI Identifier | InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5-,11-9- |
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InChI Key | HRYLQFBHBWLLLL-GYIATTAWSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Germacranolides and derivatives |
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Alternative Parents | |
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Substituents | - Germacranolide
- Germacrane sesquiterpenoid
- Sesquiterpenoid
- Gamma butyrolactone
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Lactone
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Costunolide GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-4920000000-4e64fd5fdc43499db09c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Costunolide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 10V, Positive-QTOF | splash10-001i-0390000000-90b5c48b328b46f82204 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 20V, Positive-QTOF | splash10-01qi-1930000000-6cfdc6b5c84eab2f9f7d | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 40V, Positive-QTOF | splash10-0mi6-9710000000-ddda69ef8cc562458ad9 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 10V, Negative-QTOF | splash10-001i-0290000000-07ab038b28845f8d64a1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 20V, Negative-QTOF | splash10-001r-0790000000-f2b3e216b0db2d7a4dca | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 40V, Negative-QTOF | splash10-000i-5900000000-157775eb321e2f75fa2d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 10V, Negative-QTOF | splash10-001i-0090000000-403b175a8d75af9b9dc4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 20V, Negative-QTOF | splash10-001i-0390000000-16fbf014b5978f284c85 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 40V, Negative-QTOF | splash10-01b9-9500000000-2ce7ff1d0912ac2d90ee | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 10V, Positive-QTOF | splash10-001i-0190000000-c5e9a61d3011edbf30f3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 20V, Positive-QTOF | splash10-001r-0980000000-0a8be66862e84091d6a4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Costunolide 40V, Positive-QTOF | splash10-0a4i-0900000000-9eaa625d0c4efee67791 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB015618 |
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KNApSAcK ID | C00003240 |
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Chemspider ID | 4519051 |
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KEGG Compound ID | C09382 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Costunolide |
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METLIN ID | Not Available |
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PubChem Compound | 5367559 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1016401 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Lee MG, Lee KT, Chi SG, Park JH: Costunolide induces apoptosis by ROS-mediated mitochondrial permeability transition and cytochrome C release. Biol Pharm Bull. 2001 Mar;24(3):303-6. [PubMed:11256490 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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